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418080

Sigma-Aldrich

Pentafluorophenyl diphenylphosphinate

Synonym(s):

FDPP, Diphenylphosphinic acid pentafluorophenyl ester

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About This Item

Linear Formula:
(C6H5)2P(O)OC6F5
CAS Number:
138687-69-1
Molecular Weight:
384.24
MDL number:
MFCD00192380
UNSPSC Code:
12352101
PubChem Substance ID:
24866201
NACRES:
NA.22

form

solid

mp

47-50 °C (lit.)

SMILES string

Fc1c(F)c(F)c(OP(=O)(c2ccccc2)c3ccccc3)c(F)c1F

InChI

1S/C18H10F5O2P/c19-13-14(20)16(22)18(17(23)15(13)21)25-26(24,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

InChI key

OOWSDKUFKGVADH-UHFFFAOYSA-N

General description

Pentafluorophenyl diphenylphosphinate (FDPP) is a reagent, used as a coupling agent in the amide bond forming reactions without racemization. It can also be employed in the synthesis of dipeptides with high yields and good optical purity. FDPP can be prepared from diphenylphosphinic chloride and pentafluorophenol in the presence of imidazole.

Application

Catalyst involved in coupling and macrocyclization

Reagent used in:
  • Fmoc solid-phase synthesis
  • Synthesis of phorboxazoles, furan-based cyclic homoligopeptides, and ziziphine N
FDPP can be used as a coupling reagent in the:
  • Synthesis of peptides by solid-phase and solution-phase reactions.
  • Preparation of macrocyclic peptide cyclotheonamide B as a thrombin inhibitor.
  • Cyclooligomerization of N-methylated-L-valine thiazole amino acid to obtain its cyclic tetramers.
  • Macrocyclization of an intermediate for the total synthesis of ziziphine N , and for the macrolactamization of precursor in synthesizing cryptophycin D.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Pentafluorophenyl Diphenylphosphinate (FDPP)
Leonard MS, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-8 (2001)
Pentafluorophenyl Diphenylphosphinate (FDPP).
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2002)
A new synthesis of cyclotheonamide B via guanidination of ornithine
Jingen, Deng and Yasumasa, Hamada and Takayuki, Shioiri
Tetrahedron Letters, 37(13), 2261-2264 (1996)
Pentafluorophenyl diphenylphosphinate a new efficient coupling reagent in peptide chemistry.
Chen S and Xu J
Tetrahedron Letters, 32(46), 6711-6714 (1991)
Gang He et al.
Organic letters, 9(7), 1367-1369 (2007-03-10)
[structure: see text]. A highly convergent protocol to cyclopeptide alkaloids, as demonstrated by the first total synthesis of antiplasmodial agent ziziphine N, is developed. The key elements include construction of its aryl ether unit via Mitsunobu reaction, installation of its
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